Why You Should Freelance (Despite All That Face-Punching Business)


My name is Chuck, and I remain a freelance penmonkey.

Yes, freelancing is a lot like punching yourself in the face. Over and over — and over — again. Sometimes, I feel like that animated GIF where the chimpanzee pees in his own mouth.

And yet? Here I am. Freelancing my heart out. And my pants off. No, seriously: I still haven’t put on any pants. By golly, I don’t have to. You keep your oppressive pants regime to yourself, pal. I’m fancy-free.

You want to know the other side? The not-so-sucky and sometimes downright lovely side of freelancing? It isn’t all one big masochist’s parade, after all. Fine. I can do that.

Here’s why you want to freelance despite all the self-inflicted misery:

Because You Can Watch Baby Deer Frolic From Your Office Window

I’m at a desk. The desk faces two windows. Beyond these two windows waits the forest surrounding Der Wendighaus v2.0 (yes, I have a cult-like compound in the woods, shut up). And in those woods lurk whitetail deer and their little fawn babies. I’ve seen ’em. They frolic and gambol about, and sometimes I think, “Those deer? Those deer are freelance.” Because sometimes being here, working out of the home office, that’s how I feel. Yes, I’m smashing my nose against the grindstone (so hard I’m sometimes afraid it’ll be sanded off, bzzt), but I also have ludicrous amounts of freedom in how I approach my day. The things you can’t do at your day job? I can do those things here. Crank music. Read a book for research. Drink an adult beverage. Cook myself an egg sandwich. Have long conversations with stupid dogs. I feel like the deer outside my window — dancing through the trees, taking whatever path best suits their whims.

Because Cubicles Are Like Little Prisons

I have been in many-a-cubicle. They are, regardless of their shape or construction, like little Guantanamos, little Alcatrazes. Oh, those awful gray walls forever covered in a light pubic fuzz, as if they have been covered in the pelt of some depressed Muppet. You peer out over the edge, beyond the proscribed borders — the DMZ of other desks, other 9-t0-5ers (which sounds an awful lot like other lifers) — and it’s just a sea of assholes, each trying to convince the world they’re really working when really they’re just watching nutso shit on the Internet. You know what we did with the office here? We painted it green. Crazy green. Like, dip a Granny Smith apple in a tub of uranium, then paint the liquefied fruity radioactive remains on the walls. You think you’ll get that color on your cubicle? Good luck. They’ll shoot you. Or worse, “write you up.” Someone who shall remain nameless (though her title rhymes with “Pie Strife”) works at a job where they’re moving offices, and at the new offices, the “open concept” is beyond Draconian. No pictures. No plants. No fans. No trash can. No papers on your desk. You can almost hear the clatter of keys in a lock.

Because, You Know What? Fuck The Boss

I’ve had a couple good — even great — bosses. But a lot of them were real asshats. Middle management floaters, often unaware of what those beneath them actually do, and ignorant enough that they’ve reached the pinnacles of their pbbt-thbbt mediocre careers. A lot of them micro-manage, too, which is about as much fun as a proctological exam performed by an epileptic with large, callused hands. You know who micro-manages me? Me. You know who is the boss of me? Me! Nobody else. Yes, I have clients, and yes, it is my job to meet the needs of those clients. But even the worst client is better than the best boss. You know why? That client isn’t here. He’s not standing over your shoulder. He doesn’t need a bullshit mug from you on some kind of bullshit Appreciate Your Asshole Boss Day. You don’t have to feel guilty when a client walks by your desk and you’re watching some crunchy dude in the woods go moonbat over a double rainbow. And the client will move on. You’ll have other clients. You are not slave to a single master.

Because Once In A Blue Moon, You Get To Feel Like A Goddamn Rock Star

Yesterday, we had a guy come out to look at the jury-rigged radon setup in the basement of the new house, and when I told him what I did for a living, he suddenly got very interested. What do you write? Have I read it? Do you like it? That sounds incredible. Once in a while, you’ll tell someone what you do — “I’m a freelance writer” — and they’ll get this look in their eyes like they’re looking at a crazy person. But not a dangerously crazy person — no, they see you as one of those dudes who went off the reservation to live off the grid. They look at you like you escaped. Like you tore open your straitjacket and kicked down the asylum door and ran into the woods, hooting and gibbering a hymn to sweet freedom. (See, that’s the secret: those people who pretend that freelancing isn’t a real job? Pshh, they’re just jealous.) And sometimes, sometimes you encounter someone who genuinely respects what you do, and maybe is even familiar with your work. That’s when you get a rockstar moment and it all feels really worth it.

Because You Are Like A Mutant Radiation Wolf: Hunter And Survivor

Take a look outside. No, no, look past the frolicking deer and the gibbering , hooting freelancer. What do you see? What I see is an economy that continues to try to get up out of the bed, but instead of escaping the bed all it does is defecate and throw up on itself. I see layoffs. I see rising unemployment. I see those who do have jobs made to suck a bigger pipe every day — no raises, no bonuses, health insurance costs going through the ceiling, smaller offices, shrinking cubicles, leashes tighter and tighter until one’s cheeks turn blue. It’s the apocalypse out there, folks. The freelancer, though? The freelancer isn’t a big yacht that can’t turn its ass around. The freelancer is a little boat with a big engine zig-zagging all over the place like a coke-addled water skeeter. You can turn on a dime. Big companies — and those in the belly of big companies — cannot. Freelancers adapt. One line of work dries up? Find another. Yes, you must forever be the hunter, but that means you’re a survivor, too.

Because The Tax Deductions Are Pretty Sweet

It’s a small point, but a fun one. As a writer who writes books, film, games, etc — I can buy stuff because I need it. And if I need it? I can possibly deduct it. It has limits, but I gotta tell you — when tax time comes around, it’s hard not to feel satisfied when you deduct books, games, travel.

Because You Can Get Really Good At It

If you approach it like a business? If you approach it with discipline? If you don’t spend all day drinking vodka from the bottle and rolling around in your own filth? Then hot damn, you can get pretty good at it. And you can make a living, too. And you can do it without killing yourself provided you’re willing to spend a little time on techniques to improve efficiency (again, you have to treat this like a business because, well, it is a business). When it comes time that freelance puts food in your mouth and a roof over your head, well, it doesn’t get much sweeter than that. It is the salve that heals the cuts and bruises from all that fucking face-punching. Now if you’ll excuse me, I have to go punch myself in the face and get some work done.